Substituted-2-(pyrimidinylthio)acetamidoximes and acetonitriles

Abstract

2-(6-alkyl or phenyl-2-pyrimidinylthio)acetamidoximes, in which the 4-position is substituted with the p-chlorobenzylamino, p-methoxyphenylamino, or 1,3-benzodioxol-5-yl-methylamino group, have antiarrhythmic activity. The compounds are prepared from an appropriately substituted 2-pyrimidinylthio)acetonitrile by reaction with hydroxylamine hydrochloride.

What is claimed is: 
     
       1. A compound of the formula ##SPC4## wherein R is 4-halobenzyl, 4-methoxyphenyl, or 1,3-benzodioxol-5-ylmethyl, and R 1  is methyl, ethyl, propyl, or phenyl; with the provisos that when R 1  is propyl, R cannot be 4-methoxyphenyl, and when R 1  is phenyl, R cannot be 4-halobenzyl or 4-methoxyphenyl; or a pharmaceutically acceptable acid addition salt thereof.   
     
     
       2. A compound as defined in claim 1 which is 2-[4-(p-chlorobenzylamino)-6-methyl-2-pyrimidinylthio]acetamidoxime. 
     
     
       3. A compound as defined in claim 1 which is 2-[4-(1,3-benzodioxol-4-ylmethylamino)-6-methyl-2-pyrimidinylthio]acetamidoxime. 
     
     
       4. A compound as defined in claim 1 which is 2-[4-(p-methoxyphenylamino)-6-methyl-2-pyrimidinylthio]acetamidoxime. 
     
     
       5. A compound as defined in claim 1 which is 2-[4-(p-chlorobenzylamino)-6-propyl-2-pyrimidinylthio]acetamidoxime. 
     
     
       6. A compound as defined in claim 1 which is 2-[4-(1,3-benzodioxol-5-ylmethylamino)-6-phenyl-2-pyrimidinylthio]Acetamidoxime. 
     
     
       7. A compound as defined in claim 1 which is 2-[4-(1,3-benzodioxol-5-ylmethylamino)-6-propyl-2-pyrimidinylthio]acetamidoxime. 
     
     
       8. A compound of the formula: ##SPC5## wherein R is halobenzyl, 4-methoxyphenyl, or 1,3-benzodioxol-5-ylmethyl, and R 1  is methyl, ethyl, or propyl.   
     
     
       9. a compound as defined in claim 8 which is [4-(p-chlorobenzylamino)-6-methyl-2-pyrimidinylthio]acetonitrile. 
     
     
       10. A compound as defined in claim 8 which is [4-(p-anisidino)-6-methyl-2-pyrimidinylthio]acetonitrile. 
     
     
       11. A compound as defined in claim 8 which is [4-(1,3-benzodioxol-5-ylmethylamino)-6-methyl-2-pyrimidinylthio]acetonitrile. 
     
     
       12. A compound as defined in claim 8 which is [4-(p-chlorobenzylamino)-6-propyl-2-pyrimidinylthio]acetonitrile. 
     
     
       13. A compound as defined in claim 8 which is [4-(1,3-benzodioxol-5-ylmethylamino)-6-phenyl-2-pyrimidinylthio]acetonitrile. 
     
     
       14. A compound as defined in claim 8 which is [4-(1,3-benzodioxol-5-ylmethylamino)-6-propyl-2-pyrimidinylthio]acetonitrile. 
     
     
       15. A compound of the formula: ##SPC6## wherein R is methyl, ethyl, propyl, or phenyl.   
     
     
       16. A compound as defined in claim 15 which is (4-chloro-6-methyl-2-pyrimidinylthio)acetonitrile. 
     
     
       17. A compound as defined in claim 15 which is (4-chloro-6-propyl-2-pyrimidinylthio)acetonitrile. 
     
     
       18. A compound as defined in claim 15 which is (4-chloro-6-phenyl-2-pyrimidinylthio)acetonitrile.